Leaving the Unicorn

There’s a reason that people want to work for the proverbial Silicon Valley unicorn–and it’s not the shot at the equity prize. Oh, of course, that dream is present. We all gotta eat. But most professionals who have the chops to be hired by a fast-paced startup are smart enough to recognize that they’re not the ones who are going to make a killing, even if there’s a successful exit.

No, I’m pretty sure there’s another reason–it’s the people.

I just left a unicorn after four and a half years of literally the best job of my life (yes, yes, of course my job being a parent to two beautiful children is truly the best job, but you know what I mean). And, like everyone else who left before me, it was abundantly clear by the end that what I would miss most were the people. Now, I can’t say that everyone I worked with was a soul-mate. Most weren’t. Realistically, I’m not even going to end up keeping in touch with all but a very small minority. But that’s not the point. The point is that for a blessed period of time in my life I had the privilege of working alongside smart, passionate, creative, often funny, hard-working people whose main goal every day was actually to get shit done–not push paper, not write memos, and not point fingers. And that’s really hard to leave.

I think it triggers something way back in the recesses of our evolutionary selves. Despite the fairy tale ending of the successful entrepreneurs of private jets and second houses in Vail, the reality is that life actually is work. There’s a lot of shit to do just to put food on the table, clothes on our back, and gas in the car. And since the industrial revolution, the work most of us do to put food on the table can be incredibly menial, inhuman work, that is largely devoid of meaning. (I’m sure there’s a Marxist critique in here somewhere–the division of labor, alienation, etc etc.) Frankly, there’s not a great deal of meaning, if any, in what the average blue collar or white collar laborer does from 9-5 (or 8-10) in order to put bread on the table.

The work environment in a reasonably successful tech startup, has, in ways, changed that. Of course there are shit jobs at every startup. But even the less-than-glamorous jobs are part of something that is moving, growing, breaking, fixing, heaving, and hopefully building towards a common goal. There are always more Important And Urgent things to be done than people to do them. Everyone is wearing multiple hats. Results are elevated over process. All other objectives either line up behind or get subordinated to the goal of getting a product out the door. And the teams are generally small enough for everyone to feel like they have a hand in making the company successful.

This does two things to the work environment: first, it cuts out all of the bullshit (ok, most) ; and second, it unites everyone behind a common goal.

Most startups are high-risk propositions whose continued existence is nowhere near guaranteed. The risk of failure and no longer having a paycheck are always in the back of employees’ minds, if not a daily reality. Not since we were reaping fields together under the pressure of the impending frost and fear of not having enough to eat that winter has there been a work environment in which we live so close to the bone. Yes, I’m exaggerating a bit. Point is, in that kind of environment there’s little tolerance for TPS reports.

What’s more, we live in an incredibly complex world full of forces and processes that we cannot see and cannot control. But when you come to work at a rapidly-scaling startup, all of that noise disappears, and it’s really clear what you have to do: move fast and deliver results. I used to work remotely part-time, and my 20-something co-workers laughed uneasily when I would tell them that my days in the office were like my weekend. Yes there was always a ton of work to do, but it was all focused and moving in the same direction–no interruptions from fighting kids, bills, irritating neighbors, etc. There’s a sense of freedom and pleasure in that.

The other piece, as I said, is the feeling of being united behind a common goal. So much of today’s world is fragmented and separated that we lack a sense of common cohesion in our every day lives. Hell, my wife and I have trouble connecting on a regular basis. But at work at a startup, there’s an unspoken connection that permeates all relationships–even between people who are decidedly NOT friends outside the office. Even I, a lawyer for god’s sake, was treated as a member of the team. Everyone had their area of focus, and we all understood that our individual goals for success depended on all the people around us. And so even in the hyper-self interested, “Brand Me” tech industry, there’s a kind of interdependence that, I think, feeds our souls in a way most of us probably aren’t even aware of.

I don’t mean to whitewash the darker realities of Silicon Valley or look back only with rose-colored glasses. After over a decade as a lawyer for tech startups and five of those spent in-house, I’m well-acquainted with the shadow side of all Silicon Valley–and believe me truth is indeed stranger than fiction. I guess what’s remarkable to me is that despite those shadows, when I look back at my time working for a unicorn, I see some very real, very human elements that keep people coming back to the startup world. And no matter what exactly it is, it’s just clear that after you’ve worked at a startup, the chances of you ever going to work for a behemoth company are pretty-much nil.